Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
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Synthesis of P-Stereogenic Phosphinates via an Axis-to-Center Chirality Transfer by the Reaction of Phosphonates Having a Binaphthyloxy Group with Grignard Reagents
Yuuki MaekawaKazuma KuwabaraAya SugiyamaKouji IwataToshifumi MaruyamaToshiaki Murai
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2017 Volume 46 Issue 8 Pages 1068-1071

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Abstract

The reactions of phosphonates having a binaphthyloxy group with Grignard reagents gave the corresponding P-stereogenic phosphinates in good to high yields with high diastereoselectivity. In this reaction, an axis-to-center chirality transfer from a binaphthyl group to the resulting phosphorus atom took place stereospecifically. Both diastereomers with opposite configurations could be obtained by changing the combination of carbon-containing functional groups on the phosphorus atom and the Grignard reagents.

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© 2017 The Chemical Society of Japan
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